CN106928406B - A kind of adhesive polyester of adjustable viscosity and preparation method thereof - Google Patents
A kind of adhesive polyester of adjustable viscosity and preparation method thereof Download PDFInfo
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- CN106928406B CN106928406B CN201710164997.8A CN201710164997A CN106928406B CN 106928406 B CN106928406 B CN 106928406B CN 201710164997 A CN201710164997 A CN 201710164997A CN 106928406 B CN106928406 B CN 106928406B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
- C08G63/86—Germanium, antimony, or compounds thereof
- C08G63/866—Antimony or compounds thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention provides adhesive polyester of a kind of adjustable viscosity and preparation method thereof, the adhesive is 10000-50000, acid value 1-5mg KOH/g, hydroxyl value 10-50mg KOH/g with polyester number-average molecular weight.Preparation method first passes through saturated dicarboxylic acid, the combination of unsaturated dicarboxylic acid and dihydric alcohol and carries out esterification, then obtains matrix resin by decompression polycondensation；Graft reaction finally is carried out to matrix resin, matrix resin obtained and the monomer containing azobenzene structure are subjected to graft reaction, obtain polyester.Present invention utilizes the photo-isomerisable characteristics of azobenzene, and the adhesion strength of final products is caused to reduce, and achieve the effect that composite layer separates, realize reversible adhesion repeatedly.
Description
Technical field
The invention belongs to adhesives to synthesize field, and in particular to a kind of adjustable adhesive polyester of viscosity and its preparation side
Method.
Background technique
The reversible of adhesive is bonded in many fields and all plays a very important role, and such as auto industry, semiconductor electronic, builds
It builds, secret machinery etc..
The chemical reaction that currently used method mainly passes through adhesive component is initially formed cross-linked structure, then passes through it
Its method destroys the cross-linked structure to realize.As US2005/0159521 and with light radiation irradiation radical crosslinking, so
The binding system for using ultrasound destruction afterwards, realizes reversible bonding, but after the completion of a process, cannot continue reversible implementation.
Also by the chemical structure for forming thermally labile, such as steric hindrance urea groups, then by heating, the structure is destroyed, from
And realize the decline of cohesive force.But these are irreversibly.
Summary of the invention
The present invention provides adhesive polyester of a kind of adjustable viscosity and preparation method thereof.
The purpose of the present invention is achieved through the following technical solutions:
A kind of adhesive preparation process of polyester of adjustable viscosity, includes the following steps,
S1, matrix resin is prepared, first passes through saturated dicarboxylic acid, the combination of unsaturated dicarboxylic acid and dihydric alcohol and carries out ester
Change reaction, then using decompression polycondensation, obtains matrix resin；The saturated dicarboxylic acid accounts for synthesis matrix resin total dicarboxylic acid
Total moles ratio 70-90%, the unsaturated dicarboxylic acid account for synthesis matrix resin total dicarboxylic acid total moles ratio 10-30%；
S2, graft reaction is carried out to matrix resin, by matrix resin made from S1 and the monomer containing azobenzene structure into
Row graft reaction obtains the adhesive polyester of adjustable viscosity.
Preferably, the S1 includes the following steps:
S11, saturated dicarboxylic acid, the combination of unsaturated dicarboxylic acid and dihydric alcohol are carried out being esterified instead under nitrogen atmosphere
It answers, reaction temperature is maintained between 220-255 DEG C；
S12, after the by-product of esterification in S11 reaches theoretical value, heating keep reaction temperature 250-280 DEG C it
Between, under vacuum conditions, carry out decompression polycondensation；
S13, after the completion of polycondensation reaction in S12, be filled with nitrogen and eliminate vacuum, matrix resin is made in extruding and discharging.
Preferably, the S2 includes the following steps:
S21, the solution that solid content is 50% is made in the matrix resin being prepared dissolution, initiator is added, and in nitrogen
60-70 DEG C of reaction 2h is warming up under gas shielded；
S22, to S21 product precipitation purification, the adhesive polyester of adjustable viscosity is made in vacuum drying.
Preferably, the saturated dicarboxylic acid in the S1 is selected from: terephthalic acid (TPA), M-phthalic acid, phthalic acid, third
Diacid, adipic acid, azelaic acid, decanedioic acid, phthalic anhydride, 1,4 cyclohexanedicarboxylic acid, naphthalene diacid are one such or one
Kind combination of the above.
Preferably, unsaturated dicarboxylic acid is selected from the S1: one of fumaric acid, maleic acid or more than one groups
It closes.
Preferably, dihydric alcohol is selected from the S1: ethylene glycol, 1,4-butanediol, 1,3-PD, 1,2-PD, newly
Pentanediol, hexylene glycol, 1,4-CHDM, one of polyethylene glycol or more than one combinations.
Preferably, the monomer containing azobenzene structure is selected from the S2: methacrylic acid [6- (4- Methoxy-azobenzene
Base -4 '-oxygroup) hexyl] ester, acrylic acid [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester, methacrylic acid [6-
(4- methyl- phenyl -4 '-oxygroup) hexyl] ester, methacrylic acid [6- (4- hydroxyazo phenyl -4 '-oxygroup) octyl] ester,
Methacrylic acid [6- (4- hydroxyazo phenyl -4 '-oxygroup) octyl] ester is one such or more than one are combined.
Preferably, including adhesive with polyester number-average molecular weight is 10000-50000, acid value 1-5mg KOH/g, hydroxyl value
10-50mg KOH/g。
The present invention is that azobenzene structure polymer is widely closed due to its unique photo-isomerisable performance using principle
Note, in optics, crystal structure, gel etc. has all multipurposes.Azobenzene polymer can occur under the irradiation of light can
Inverse cis-trans isomerism, structure and performance to polymer have very big influence, especially optical property and crystal property,
The glass transition temperature that can also influence polymer simultaneously, changes the form of polymer, changes the cohesive force and chain of glue-line
Section arrangement can so realize the viscosity control of adhesive at room temperature by illumination.
The beneficial effects of the present invention are embodied in: synthesis branch has the polyester adhesive resin of azobenzene, utilizes azo
The photo-isomerisable characteristic of benzene: in the case where wavelength is 540nm illumination, azobenzene is the very strong transconfiguration of rigidity, and product vitrifying turns
Temperature is relatively high, there is preferable cohesive force and adhesion strength；And after using wavelength 365nm treatment with ultraviolet light, azobenzene
By it is trans- switch to it is cis-, the glass transition temperature of product drop to room temperature hereinafter, at room temperature have certain viscoelastic
Property, to change the variation of molecule arranging structure, decline cohesive force, the adhesion strength of product is caused to reduce, reaches composite layer
Isolated effect realizes reversible adhesion repeatedly.
Specific embodiment
It is specifically described technical solution of the present invention with reference to embodiments.
The synthesis of adhesive resin
Example one
A), the preparation of polyester matrix resin:
By 1.66kg terephthalic acid (TPA), 3.32kg M-phthalic acid, 7.31kg adipic acid, 2.32kg maleic acid, 6.08kg
Ethylene glycol, 4.96kg hexylene glycol and 4.4g isopropyl titanate are put into reaction kettle.Discharge air is replaced with nitrogen, stirring rises
Temperature is to carrying out esterification between 220-255 DEG C.After by-product reaches theoretical value, heating keeps reaction temperature in 250-280
Between DEG C, polycondensation is depressurized, stops reaction after reaching terminal, nitrogen is filled with and eliminates vacuum, extruding and discharging obtains matrix resin.
B), graft reaction:
The matrix resin being prepared is dissolved in butanone, the solution of solid content 50% is made, 16g initiator is added
Azodiisobutyronitrile, 7.92kg methacrylic acid [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester are uniformly mixed, so
Afterwards under the protection of nitrogen, it is warming up to 60-70 DEG C of reaction 2h.After n-hexane precipitation purification, vacuum drying obtains adhesive use
Polyester.
Example two
A), the preparation of polyester matrix resin:
By 1.66kg terephthalic acid (TPA), 3.32kg M-phthalic acid, 10.1kg decanedioic acid, 2.32kg maleic acid, 6.08kg
Ethylene glycol, 4.37kg neopentyl glycol and 3.5g antimony acetate are put into reaction kettle.Discharge air, stirring heating are replaced with nitrogen
Esterification is carried out between to 220-255 DEG C.After by-product reaches theoretical value, heating keeps reaction temperature at 250-280 DEG C
Between, polycondensation is depressurized, stops reaction after reaching terminal, nitrogen is filled with and eliminates vacuum, extruding and discharging obtains matrix resin.
B), graft reaction:
The matrix resin being prepared is dissolved in toluene, the solution of solid content 50% is made, 16g initiator is added
Azodiisobutyronitrile, 9.53kg acrylic acid [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester are uniformly mixed, then exist
Under the protection of nitrogen, it is warming up to 60-70 DEG C of reaction 2h.After n-hexane precipitation purification, vacuum drying obtains adhesive polyester.
Example three
A), the preparation of polyester matrix resin:
By 4.15kg M-phthalic acid, 10.1kg decanedioic acid, 2.9kg fumaric acid, 11.5kg hexylene glycol, 4.37kg new penta 2
Alcohol and 3.5g antimony acetate are put into reaction kettle.Discharge air is replaced with nitrogen, stirring, which is warming up between 220-255 DEG C, to be carried out
Esterification.After by-product reaches theoretical value, heating keeps reaction temperature between 250-280 DEG C, depressurizes polycondensation, reaches eventually
Stop reaction after point, is filled with nitrogen and eliminates vacuum, extruding and discharging obtains matrix resin.
B), graft reaction:
The matrix resin being prepared is dissolved in butanone, the solution of solid content 50% is made, 16g initiator is added
Azodiisobutyronitrile, 9.53kg acrylic acid [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester are uniformly mixed, then exist
Under the protection of nitrogen, it is warming up to 60-70 DEG C of reaction 2h.After n-hexane precipitation purification, vacuum drying obtains adhesive polyester
Example four
A), the preparation of polyester matrix resin:
By 4.15kg1,4- cyclohexane cyclohexanedimethanodibasic, 10.1kg decanedioic acid, 3.48kg fumaric acid, 11.6kg1,4- butanediol,
4.37kg neopentyl glycol and 3.5g antimony acetate are put into reaction kettle.Discharge air is replaced with nitrogen, stirring is warming up to 220-
Esterification is carried out between 255 DEG C.After by-product reaches theoretical value, heating keeps reaction temperature between 250-280 DEG C, subtracts
Compression is poly-, stops reaction after reaching terminal, is filled with nitrogen and eliminates vacuum, extruding and discharging obtains matrix resin.
B), graft reaction:
The matrix resin being prepared is dissolved in butanone, the solution of solid content 50% is made, 16g initiator is added
Azodiisobutyronitrile, 9.18kg methacrylic acid [6- (4- hydroxyazo phenyl -4 '-oxygroup) octyl] ester are uniformly mixed, then
Under the protection of nitrogen, it is warming up to 60-70 DEG C of reaction 2h.After n-hexane precipitation purification, it is poly- that vacuum drying obtains adhesive use
Ester.
Comparative example
By 4.15kg1,4- cyclohexane cyclohexanedimethanodibasic, 10.1kg decanedioic acid, 3.48kg fumaric acid, 11.6kg1,4- butanediol,
4.37kg neopentyl glycol and 3.5g antimony acetate are put into reaction kettle.Discharge air is replaced with nitrogen, stirring is warming up to 220-
Esterification is carried out between 255 DEG C.After by-product reaches theoretical value, heating keeps reaction temperature between 250-280 DEG C, subtracts
Compression is poly-, stops reaction after reaching terminal, is filled with nitrogen and eliminates vacuum, extruding and discharging obtains comparative example resin.
The measurement of number-average molecular weight
Utilize GPC(gel permeation chromatography) measurement polymer number-average molecular weight, surveyed using waters company GPC
Fixed, at 30 DEG C in tetrahydrofuran (THF), relatively a series of polystyrene standards carry out the measurement.
The test of glass transition temperature
It is tested using the DSC of TA company, test sample is 540nm, light intensity 5mW*cm in wavelength respectively-2Light at
After reason, and first time light irradiation after be again 365nm, light intensity 70mW*cm with wavelength-2Ultraviolet light 20min after
Glass transition temperature (Tg).
Sample is apparently observed
Apparent condition of the sample after lighting process twice is observed by the naked eye, and is pressed with hand and touches the flowing of its hardness
Property.
The results are shown in Table 1 for the above test performance.
Table 1: embodiment and comparative example product index compare:
| Number | Number-average molecular weight | Tg (irradiates) for the first time | Tg (second of irradiation) |
| Embodiment one | 12000 | 23℃ | -15℃ |
| Embodiment two | 35000 | 40℃ | 5.8℃ |
| Embodiment three | 40000 | 32℃ | -7.5℃ |
| Example IV | 22000 | 36℃ | -21℃ |
| Comparative example | 30000 | 32℃ | 32℃ |
It is obtained from above data, analyzed by the glass transition temperature for adhesion layer sample after light processing, sample exists
After 540nm lighting process, azobenzene structure is transconfiguration (trans), and integral rigidity is very strong, so glass transition temperature ratio
Higher, sample keeps solid state at room temperature, and cohesive force is stronger.Then photo-isomerisable occurs with after treatment with ultraviolet light again,
Azobenzene structure treated for the first time it is trans- switch to cis- (cis), whole Tg is reduced, and is lower than room temperature, at this time adhesion layer resin
There is certain mobile performance at room temperature, segment activity, cohesive force reduces, so that adhesion property reduces, composite layer is easy
Separation.
Adhesion test
The resin of four embodiment and comparative examples is subjected to compound, the tree that will be obtained with PET film and tinplate sheet respectively
Rouge is dissolved in ethyl acetate solvent, is configured to the solution of solid content 30%, is then coated on tinplate, and solid content is glued
For 10g/m2, then polyethylene terephthalate (PET) film of composite transparent is 10 minutes dry at 80 DEG C, first uses wavelength
For 540nm, light intensity 5mW*cm-2Light irradiation 20min after, cut 15mm × 200mm batten, use tensile strength test
Machine carries out 180 ° of disbonded tests at 25 DEG C with the test speed of 50mm/min.
It is 365nm, light intensity 70mW*cm that the composite layer crossed through first time treatment with irradiation, which is used wavelength,-2Ultraviolet lighting
It penetrates 20min and carries out second for the treatment of with irradiation, the batten of 15mm × 200mm is then cut to, using instron, 25
DEG C, 180 ° of disbonded tests are carried out with the test speed of 50mm/min, are compared as shown in table 2.
Table 2: embodiment and comparative example product property compare:
| Number | Peeling force (N/mm) after first time lighting process | Peeling force (N/mm) after second of lighting process |
| Embodiment one | 3.7 | 0.7 |
| Embodiment two | 4.5 | 0.4 |
| Embodiment three | 4.2 | 0.65 |
| Example IV | 4.4 | 0.9 |
| Comparative example | 4.2 | 4.2 |
By the test analysis of the peeling force after different lighting processes, after first time lighting process, composite layer has
Preferable peel strength, sample adhesion strength are stronger.After second of lighting process, since the structure of sample changes,
Peeling force greatly reduces, and composite layer can be separated easily, is reprocessed.
Still there are many specific embodiments by the present invention.All all skills formed using equivalent replacement or equivalent transformation
Art scheme, all falls within the scope of protection of present invention.
Claims (7)
1. a kind of adhesive preparation process of polyester of adjustable viscosity, it is characterised in that: include the following steps,
S1, matrix resin is prepared, first passes through saturated dicarboxylic acid, the combination of unsaturated dicarboxylic acid and dihydric alcohol and be esterified instead
It answers, then using decompression polycondensation, obtains matrix resin；The saturated dicarboxylic acid accounts for synthesis matrix resin total dicarboxylic acid and always rubs
You are ratio 70-90%, and the unsaturated dicarboxylic acid accounts for synthesis matrix resin total dicarboxylic acid total moles ratio 10-30%；
S2, graft reaction is carried out to matrix resin, matrix resin made from S1 and the monomer containing azobenzene structure is connect
Branch reaction, obtains the adhesive polyester of adjustable viscosity；
The S1 includes the following steps:
S11, saturated dicarboxylic acid, the combination of unsaturated dicarboxylic acid and dihydric alcohol are subjected to esterification under nitrogen atmosphere,
Reaction temperature is maintained between 220-255 DEG C；
S12, after the by-product of esterification in S11 reaches theoretical value, heating keep reaction temperature between 250-280 DEG C,
Under vacuum conditions, decompression polycondensation is carried out；
S13, after the completion of polycondensation reaction in S12, be filled with nitrogen and eliminate vacuum, matrix resin is made in extruding and discharging.
2. a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, it is characterised in that: the S2 packet
Include following steps:
S21, the solution that solid content is 50% is made in the matrix resin being prepared dissolution, initiator is added, and protect in nitrogen
60-70 DEG C of reaction 2h is warming up under shield；
S22, to S21 product precipitation purification, the adhesive polyester of adjustable viscosity is made in vacuum drying.
3. a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, it is characterised in that: in the S1
Saturated dicarboxylic acid be selected from: terephthalic acid (TPA), M-phthalic acid, phthalic acid, malonic acid, adipic acid, azelaic acid, the last of the ten Heavenly stems two
Acid, phthalic anhydride, 1,4 cyclohexanedicarboxylic acid, naphthalene diacid are one such or more than one are combined.
4. a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, it is characterised in that: in the S1
Unsaturated dicarboxylic acid is selected from: one of fumaric acid, maleic acid or more than one combinations.
5. a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, it is characterised in that: in the S1
Dihydric alcohol is selected from: ethylene glycol, 1,4-butanediol, 1,3-PD, 1,2-PD, neopentyl glycol, hexylene glycol, Isosorbide-5-Nitrae-hexamethylene
Dimethanol, one of polyethylene glycol or more than one combinations.
6. a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, it is characterised in that: in the S2
Monomer containing azobenzene structure is selected from: methacrylic acid [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester, propylene
Sour [6- (4- Methoxy-azobenzene base -4 '-oxygroup) hexyl] ester, methacrylic acid [6- (4- methyl- phenyl -4 '-oxygroup)
Hexyl] ester, methacrylic acid [6- (4- hydroxyazo phenyl -4 '-oxygroup) octyl] ester, methacrylic acid [6- (4- hydroxyazo
Phenyl -4 '-oxygroup) octyl] ester is one such or more than one are combined.
7. polyester made from a kind of adhesive preparation process of polyester of adjustable viscosity as described in claim 1, feature exist
In: the adhesive is 10000-50000, acid value 1-5mg KOH/g, hydroxyl value 10-50mg KOH/g with polyester number-average molecular weight.
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| CN109666438B (en) * | 2018-12-21 | 2020-09-01 | 广州市白云化工实业有限公司 | Photo-responsive adhesive and preparation method thereof |
| CN109652000B (en) * | 2018-12-21 | 2021-08-31 | 广州市白云化工实业有限公司 | Novel electronic printed circuit board coating adhesive and preparation method thereof |
| US20200263088A1 (en) * | 2019-02-14 | 2020-08-20 | Konica Minolta, Inc. | Photoresponsive high-molecular weight material, adhesive, toner, and image forming method |
| CN113817146A (en) * | 2021-08-09 | 2021-12-21 | 浙江乘鹰新材料股份有限公司 | Polyester resin and preparation method and application thereof |
| CN114031759A (en) * | 2021-12-10 | 2022-02-11 | 盐城市恒丰海绵有限公司 | Unsaturated fatty diacid-based polyester polyol and preparation method thereof |
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